JPH0449544B2 - - Google Patents
Info
- Publication number
- JPH0449544B2 JPH0449544B2 JP58017556A JP1755683A JPH0449544B2 JP H0449544 B2 JPH0449544 B2 JP H0449544B2 JP 58017556 A JP58017556 A JP 58017556A JP 1755683 A JP1755683 A JP 1755683A JP H0449544 B2 JPH0449544 B2 JP H0449544B2
- Authority
- JP
- Japan
- Prior art keywords
- cyanopyridine
- reaction
- oxide
- mol
- chloro
- Prior art date
- Legal status (The legal status is an assumption and is not a legal conclusion. Google has not performed a legal analysis and makes no representation as to the accuracy of the status listed.)
- Expired - Lifetime
Links
- XHXFXVLFKHQFAL-UHFFFAOYSA-N phosphoryl trichloride Chemical compound ClP(Cl)(Cl)=O XHXFXVLFKHQFAL-UHFFFAOYSA-N 0.000 claims description 36
- USSFUVKEHXDAPM-UHFFFAOYSA-N Nicotinamide N-oxide Chemical compound NC(=O)C1=CC=C[N+]([O-])=C1 USSFUVKEHXDAPM-UHFFFAOYSA-N 0.000 claims description 20
- JAUPUQRPBNDMDT-UHFFFAOYSA-N 2-chloropyridine-3-carbonitrile Chemical compound ClC1=NC=CC=C1C#N JAUPUQRPBNDMDT-UHFFFAOYSA-N 0.000 claims description 17
- IBRSSZOHCGUTHI-UHFFFAOYSA-N 2-chloropyridine-3-carboxylic acid Chemical compound OC(=O)C1=CC=CN=C1Cl IBRSSZOHCGUTHI-UHFFFAOYSA-N 0.000 claims description 14
- MHAJPDPJQMAIIY-UHFFFAOYSA-N Hydrogen peroxide Chemical compound OO MHAJPDPJQMAIIY-UHFFFAOYSA-N 0.000 claims description 12
- GZPHSAQLYPIAIN-UHFFFAOYSA-N 3-pyridinecarbonitrile Chemical compound N#CC1=CC=CN=C1 GZPHSAQLYPIAIN-UHFFFAOYSA-N 0.000 claims description 11
- 238000004519 manufacturing process Methods 0.000 claims description 5
- 229910044991 metal oxide Inorganic materials 0.000 claims description 4
- 150000004706 metal oxides Chemical class 0.000 claims description 4
- 239000003125 aqueous solvent Substances 0.000 claims description 2
- 230000003301 hydrolyzing effect Effects 0.000 claims description 2
- 238000006243 chemical reaction Methods 0.000 description 36
- 239000013078 crystal Substances 0.000 description 21
- OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 18
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 18
- OKTJSMMVPCPJKN-UHFFFAOYSA-N Carbon Chemical compound [C] OKTJSMMVPCPJKN-UHFFFAOYSA-N 0.000 description 14
- 238000000034 method Methods 0.000 description 10
- HEMHJVSKTPXQMS-UHFFFAOYSA-M Sodium hydroxide Chemical compound [OH-].[Na+] HEMHJVSKTPXQMS-UHFFFAOYSA-M 0.000 description 9
- 238000010521 absorption reaction Methods 0.000 description 7
- 238000002844 melting Methods 0.000 description 7
- 230000008018 melting Effects 0.000 description 7
- 239000000203 mixture Substances 0.000 description 6
- 238000001816 cooling Methods 0.000 description 5
- 239000000047 product Substances 0.000 description 5
- 238000010992 reflux Methods 0.000 description 5
- VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 description 4
- 238000000354 decomposition reaction Methods 0.000 description 4
- 238000010438 heat treatment Methods 0.000 description 4
- 150000003512 tertiary amines Chemical class 0.000 description 4
- FFNVQNRYTPFDDP-UHFFFAOYSA-N 2-cyanopyridine Chemical compound N#CC1=CC=CC=N1 FFNVQNRYTPFDDP-UHFFFAOYSA-N 0.000 description 3
- YXFVVABEGXRONW-UHFFFAOYSA-N Toluene Chemical compound CC1=CC=CC=C1 YXFVVABEGXRONW-UHFFFAOYSA-N 0.000 description 3
- ZMANZCXQSJIPKH-UHFFFAOYSA-N Triethylamine Chemical compound CCN(CC)CC ZMANZCXQSJIPKH-UHFFFAOYSA-N 0.000 description 3
- 150000001875 compounds Chemical class 0.000 description 3
- 230000007062 hydrolysis Effects 0.000 description 3
- 238000006460 hydrolysis reaction Methods 0.000 description 3
- 239000002904 solvent Substances 0.000 description 3
- PVNIIMVLHYAWGP-UHFFFAOYSA-N Niacin Chemical compound OC(=O)C1=CC=CN=C1 PVNIIMVLHYAWGP-UHFFFAOYSA-N 0.000 description 2
- JUJWROOIHBZHMG-UHFFFAOYSA-N Pyridine Chemical compound C1=CC=NC=C1 JUJWROOIHBZHMG-UHFFFAOYSA-N 0.000 description 2
- QAOWNCQODCNURD-UHFFFAOYSA-N Sulfuric acid Chemical compound OS(O)(=O)=O QAOWNCQODCNURD-UHFFFAOYSA-N 0.000 description 2
- 239000007795 chemical reaction product Substances 0.000 description 2
- 239000007788 liquid Substances 0.000 description 2
- FJCFFCXMEXZEIM-UHFFFAOYSA-N oxiniacic acid Chemical compound OC(=O)C1=CC=C[N+]([O-])=C1 FJCFFCXMEXZEIM-UHFFFAOYSA-N 0.000 description 2
- 239000007858 starting material Substances 0.000 description 2
- RXTRRIFWCJEMEL-UHFFFAOYSA-N 2-chloropyridine-3-carbonyl chloride Chemical compound ClC(=O)C1=CC=CN=C1Cl RXTRRIFWCJEMEL-UHFFFAOYSA-N 0.000 description 1
- ITQTTZVARXURQS-UHFFFAOYSA-N 3-methylpyridine Chemical compound CC1=CC=CN=C1 ITQTTZVARXURQS-UHFFFAOYSA-N 0.000 description 1
- 229910004803 Na2 WO4.2H2 O Inorganic materials 0.000 description 1
- CTQNGGLPUBDAKN-UHFFFAOYSA-N O-Xylene Chemical compound CC1=CC=CC=C1C CTQNGGLPUBDAKN-UHFFFAOYSA-N 0.000 description 1
- CYTYCFOTNPOANT-UHFFFAOYSA-N Perchloroethylene Chemical group ClC(Cl)=C(Cl)Cl CYTYCFOTNPOANT-UHFFFAOYSA-N 0.000 description 1
- XSTXAVWGXDQKEL-UHFFFAOYSA-N Trichloroethylene Chemical group ClC=C(Cl)Cl XSTXAVWGXDQKEL-UHFFFAOYSA-N 0.000 description 1
- 239000002253 acid Substances 0.000 description 1
- 238000005903 acid hydrolysis reaction Methods 0.000 description 1
- 230000002378 acidificating effect Effects 0.000 description 1
- 239000003513 alkali Substances 0.000 description 1
- 229910052783 alkali metal Inorganic materials 0.000 description 1
- -1 alkali metal salts Chemical class 0.000 description 1
- 150000001412 amines Chemical class 0.000 description 1
- 150000003863 ammonium salts Chemical class 0.000 description 1
- 230000000202 analgesic effect Effects 0.000 description 1
- 150000004945 aromatic hydrocarbons Chemical class 0.000 description 1
- 238000009835 boiling Methods 0.000 description 1
- 150000001732 carboxylic acid derivatives Chemical class 0.000 description 1
- 239000007810 chemical reaction solvent Substances 0.000 description 1
- 238000004040 coloring Methods 0.000 description 1
- 238000007796 conventional method Methods 0.000 description 1
- YWEUIGNSBFLMFL-UHFFFAOYSA-N diphosphonate Chemical compound O=P(=O)OP(=O)=O YWEUIGNSBFLMFL-UHFFFAOYSA-N 0.000 description 1
- 239000003814 drug Substances 0.000 description 1
- 150000008282 halocarbons Chemical class 0.000 description 1
- 239000000543 intermediate Substances 0.000 description 1
- VLAPMBHFAWRUQP-UHFFFAOYSA-L molybdic acid Chemical compound O[Mo](O)(=O)=O VLAPMBHFAWRUQP-UHFFFAOYSA-L 0.000 description 1
- VIJMMQUAJQEELS-UHFFFAOYSA-N n,n-bis(ethenyl)ethenamine Chemical compound C=CN(C=C)C=C VIJMMQUAJQEELS-UHFFFAOYSA-N 0.000 description 1
- 235000001968 nicotinic acid Nutrition 0.000 description 1
- 239000011664 nicotinic acid Substances 0.000 description 1
- 229960003512 nicotinic acid Drugs 0.000 description 1
- 239000012450 pharmaceutical intermediate Substances 0.000 description 1
- DLYUQMMRRRQYAE-UHFFFAOYSA-N phosphorus pentoxide Inorganic materials O1P(O2)(=O)OP3(=O)OP1(=O)OP2(=O)O3 DLYUQMMRRRQYAE-UHFFFAOYSA-N 0.000 description 1
- 238000000746 purification Methods 0.000 description 1
- UMJSCPRVCHMLSP-UHFFFAOYSA-N pyridine Natural products COC1=CC=CN=C1 UMJSCPRVCHMLSP-UHFFFAOYSA-N 0.000 description 1
- 239000011541 reaction mixture Substances 0.000 description 1
- 238000001953 recrystallisation Methods 0.000 description 1
- QYHFIVBSNOWOCQ-UHFFFAOYSA-N selenic acid Chemical compound O[Se](O)(=O)=O QYHFIVBSNOWOCQ-UHFFFAOYSA-N 0.000 description 1
- XMVONEAAOPAGAO-UHFFFAOYSA-N sodium tungstate Chemical compound [Na+].[Na+].[O-][W]([O-])(=O)=O XMVONEAAOPAGAO-UHFFFAOYSA-N 0.000 description 1
- 238000003756 stirring Methods 0.000 description 1
- 229950011008 tetrachloroethylene Drugs 0.000 description 1
- LLZRNZOLAXHGLL-UHFFFAOYSA-J titanic acid Chemical compound O[Ti](O)(O)O LLZRNZOLAXHGLL-UHFFFAOYSA-J 0.000 description 1
- CMPGARWFYBADJI-UHFFFAOYSA-L tungstic acid Chemical compound O[W](O)(=O)=O CMPGARWFYBADJI-UHFFFAOYSA-L 0.000 description 1
- LSGOVYNHVSXFFJ-UHFFFAOYSA-N vanadate(3-) Chemical compound [O-][V]([O-])([O-])=O LSGOVYNHVSXFFJ-UHFFFAOYSA-N 0.000 description 1
- 238000005406 washing Methods 0.000 description 1
- 239000008096 xylene Substances 0.000 description 1
Landscapes
- Pyridine Compounds (AREA)
Priority Applications (1)
Application Number | Priority Date | Filing Date | Title |
---|---|---|---|
JP1755683A JPS59144759A (ja) | 1983-02-07 | 1983-02-07 | 2−クロロニコチン酸の製造方法 |
Applications Claiming Priority (1)
Application Number | Priority Date | Filing Date | Title |
---|---|---|---|
JP1755683A JPS59144759A (ja) | 1983-02-07 | 1983-02-07 | 2−クロロニコチン酸の製造方法 |
Publications (2)
Publication Number | Publication Date |
---|---|
JPS59144759A JPS59144759A (ja) | 1984-08-18 |
JPH0449544B2 true JPH0449544B2 (de) | 1992-08-11 |
Family
ID=11947184
Family Applications (1)
Application Number | Title | Priority Date | Filing Date |
---|---|---|---|
JP1755683A Granted JPS59144759A (ja) | 1983-02-07 | 1983-02-07 | 2−クロロニコチン酸の製造方法 |
Country Status (1)
Country | Link |
---|---|
JP (1) | JPS59144759A (de) |
Families Citing this family (8)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
DE3840954A1 (de) * | 1988-12-05 | 1990-06-07 | Shell Int Research | Herstellung von 2-chlornicotinsaeureestern |
CN103408489A (zh) * | 2013-08-29 | 2013-11-27 | 武穴市永宁医药化工有限公司 | 一种3-氰基吡啶氮氧化物的制备方法 |
CN103570617B (zh) * | 2013-11-15 | 2016-05-04 | 浙江荣凯科技发展股份有限公司 | 一种3-氰基-吡啶n-氧化物的制备方法 |
CN104072409B (zh) * | 2014-06-27 | 2016-08-24 | 温州大学 | 一种吡啶酰胺类化合物的合成方法 |
CN109438340A (zh) * | 2018-10-25 | 2019-03-08 | 老河口市天和科技有限公司 | 一种2-氯-3-氰基吡啶的制备工艺 |
CN110790701B (zh) * | 2019-09-29 | 2021-09-03 | 江苏三鹏生物化工有限公司 | 一种利用腈化合物水解制备羧酸的工艺 |
CN113149903B (zh) * | 2021-04-30 | 2023-02-10 | 安徽国星生物化学有限公司 | 一种氰基吡啶的合成方法及装置 |
CN116903527A (zh) * | 2023-06-19 | 2023-10-20 | 湖北进创博生物科技有限公司 | 一种基于贵金属纺丝催化布的2-氯烟酸合成方法 |
Citations (4)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
JPS4867282A (de) * | 1971-12-16 | 1973-09-13 | ||
JPS4880570A (de) * | 1972-02-04 | 1973-10-29 | ||
JPS4881867A (de) * | 1972-02-15 | 1973-11-01 | ||
JPS56169672A (en) * | 1980-06-02 | 1981-12-26 | Koei Chem Co Ltd | Preparation of 2-chloro-3-cyanopyridine and 2- chloronicotinic acid |
-
1983
- 1983-02-07 JP JP1755683A patent/JPS59144759A/ja active Granted
Patent Citations (4)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
JPS4867282A (de) * | 1971-12-16 | 1973-09-13 | ||
JPS4880570A (de) * | 1972-02-04 | 1973-10-29 | ||
JPS4881867A (de) * | 1972-02-15 | 1973-11-01 | ||
JPS56169672A (en) * | 1980-06-02 | 1981-12-26 | Koei Chem Co Ltd | Preparation of 2-chloro-3-cyanopyridine and 2- chloronicotinic acid |
Also Published As
Publication number | Publication date |
---|---|
JPS59144759A (ja) | 1984-08-18 |
Similar Documents
Publication | Publication Date | Title |
---|---|---|
JPH0449544B2 (de) | ||
CN111285800B (zh) | 一种氨氯吡啶酸废渣的处理方法 | |
US3274206A (en) | Process for the production of pyridine aldehydes | |
CA2141046C (en) | Improved process for the synthesis of 2,6-dichloro-5-fluoronicotinic acid and 2,6-dichloro-5-fluoronicotinoyl chloride | |
IE57308B1 (en) | A method for oxidizing alkyl groups to carboxylic acids under basic conditions | |
JP3858876B2 (ja) | 窒素含有芳香族ヘテロ環化合物カルボキサミドから対応するカルボン酸を製造する方法 | |
EP0092117B1 (de) | Verfahren zur Herstellung von Chlornikotinsäure-Verbindungen | |
EP1424328B1 (de) | Verfahren zur Herstellung von 4-Dimethylaminopyridin (4-DMAP) | |
KR100229177B1 (ko) | 2-클로로피리딘의 제조방법 | |
DK163184B (da) | Fremgangsmaade til fremstilling af 2-carbamoyl-nicotin- og -3-quinolincarboxylsyrer | |
US2109954A (en) | Oxidation of alkyl pyridines and alkyl quinolines | |
JP3315219B2 (ja) | 置換された硝酸2,3−ジカルボキシピリジニウム | |
JPS632262B2 (de) | ||
JP3315220B2 (ja) | 2,3−ピリジンジカルボン酸及びその誘導体の改善された製造方法 | |
JPH0557270B2 (de) | ||
JP2563432B2 (ja) | クロロ―2―ピリジノールの製造方法 | |
JPS58174366A (ja) | ハロピリジン類の酸化方法 | |
JPH03223252A (ja) | 置換メチルアミン類の製造方法 | |
JP3158599B2 (ja) | 新規な5−メトキシ−2−[[(4−メトキシ−3,5−ジメチル−2−ピリジル)メチル]チオ]イミダゾ[4,5−b]ピリジンの製造方法並びにその製造中間体及びその製造方法 | |
JPH07304726A (ja) | 2−アリール−エタン−スルホン酸類の製造方法 | |
JPH0987251A (ja) | モノ−およびジ−シアノピリジン−n−オキシドの製造方法 | |
US2748137A (en) | Process for preparing isonicotinic acid | |
JPH0645598B2 (ja) | ヒドロキシメチルピリジンの製造方法 | |
JPH05125047A (ja) | 2−クロルピリジンの製法 | |
JP3790290B2 (ja) | 第三級アミンn−オキシドの製造方法 |